A Cascade Reaction Consisting of Pictet-Spengler-Type Cyclization and Smiles Rearrangement: Application to the Synthesis of Novel Pyrrole-Fused Dihydropteridines

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• 作者：Jinbao Xiang ; Lianyou Zheng ; Feng Chen ; Qun Dang ; Xu Bai
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：March 1, 2007
• 年：2007
• 卷：9
• 期：5
• 页码：765 - 767
• 全文大小：63K
• 年卷期：v.9,no.5(March 1, 2007)
• ISSN：1523-7052

文摘

Tandem Pictet-Spengler-type cyclization and Smiles rearrangement have been discovered in the synthesis of pyrimidine-fused heterocycles.The reaction of 4-chloro-5-pyrrol-1-ylpyrimidine amino aldehyde with an amine under an acidic condition yielded the Pictet-Spengler-typecyclization product diazepine, which readily underwent Smiles rearrangement to give a novel pyrrolo[1,2-f]pteridine derivative.